Acetamide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Acetamide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Acetamide?

The molecule Acetamide presents a molecular formula of C2H5NO and its IUPAC name is acetamide.

Acetamide is a molecule with the chemical formula CH3C(O)NH2. It is a colorless liquid that is miscible with water and has a slightly unpleasant odor. Acetamide is a member of the amide class of compounds and lies as a weak acid..

The molecule consists of a central carbon atom bonded to two hydrogen atoms and an oxygen atom. The carbon atom is also bonded to a nitrogen atom via a double bond. The structure of acetamide is similar to that of acetic acid, except that the hydrogen atom bonded to the oxygen atom is replaced by a nitrogen atom..

The boiling point of acetamide is 117°C and the melting point is -45°C. The molecule is soluble in water and has a density of 0.917 g/cm3..

Acetamide is produced industrially by the amination of acetic acid. It is used as a starting material for the synthesis of other chemicals, such as acetaminophen and acetonitrile. It is also used as a solvent and as a plasticizer..

Acetamide is a weak acid, with a pKa of 4.75. This means that it is only partially dissociated in water. The molecule is protonated at the nitrogen atom in acidic solution and deprotonated in basic solution..

The molecule is planar and has a dipole moment of 2.13 D. The carbon atom is the center of chirality and the molecule has two optical isomers, designated as (R)- and (S)-acetamide..

The (R)-isomer is the more stable of the two and is the form that belongs in nature. The (S)-isomer is less stable and is less abundant in nature..

Acetamide is used as a starting material in the synthesis of other chemicals. It is also used as a solvent and as a plasticizer..

3D structure

Cartesian coordinates

Geometry of Acetamide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Acetamide DLFVBJFMPXGRIB-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Acetamide

 

Molecule descriptors

 
IUPAC nameacetamide
InChI codeInChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
InChI KeyDLFVBJFMPXGRIB-UHFFFAOYSA-N
SMILESC(=O)(N)C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:

Physico-Chemical properties

IUPAC nameacetamide
Molecular formulaC2H5NO
Molecular weight59.0672
Melting point (ºC)80
Boiling point (ºC)221
Density (g/cm3)-
Molar refractivity14.64
LogP0.2
Topological polar surface area37.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.